Your third picture has an event tracker at the top left corner. I can't see all of it, but what I can see is that the event's title ends with the word Problem. This, along with the description of the trouble you're having, makes me think that you do have No Skills, No Problem as an active challenge scenario for that save. Here's the description of No Skills, No Problem from the game itself:
A sim cannot seem to get skillful at... well, anything! It's made everything more difficult, from relationships to holding a steady job, and, as a result, they've had to figure out ways to work harder or smarter than everyone else. Can this unskilled Sim figure out how to hack life and earn some sweet Simoleons?
The actual effect of the challenge is to prevent the affected Sim from gaining any skills, just as you described. The solution is to either complete the challenge, by having 400,000 Simoleons, or cancel the challenge by clicking the trashcan button at the bottom of its event tracker.